


Dean Winchester's Very Own Advent Calendar

by Cerdic519



Series: A Very Destiel Christmas [1]
Category: Supernatural
Genre: Advent Calendar, Anal Sex, Barista Dean, Batman but not Batman, Blow Jobs, Castiel in Panties, Cowboy Castiel, Cuddling & Snuggling, Dean Loves Pie, Dean in Panties, Destiel - Freeform, Dildos, Doctor Castiel, Episode: s04e01 Lazarus Rising, Gay Sex, Happy Ending, Heaven, Knotting, LARPing, Librarian Castiel, M/M, Marriage Proposal, Medical Patient Dean, Modeling, Pteruges, Restraints, Sex Pollen, Shower Sex, Star Trek References, Teasing, Tooth-Rotting Fluff, Vibrators
Language: English
Status: Completed
Published: 2015-11-30
Updated: 2015-12-25
Packaged: 2018-05-04 04:46:01
Rating: Mature
Warnings: No Archive Warnings Apply
Chapters: 26
Words: 12,201
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/5320991
Author URL: https://archiveofourown.org/users/Cerdic519/pseuds/Cerdic519
Summary: <blockquote class="userstuff">
              <p>To mark the festive season, the angel decides to give the love of his life a very special Advent calendar. It contains a bit more than miniature chocolates.....</p>
            </blockquote>





	1. Prologue

In the end, it was all very simple.

After the Darkness was conquered, Rowena had been consigned to some distant set of netherworld dimensions, and best of all, Metadouche had been reduced to a pile of black sludge (coincidentally Dean's mobile picture), the Winchesters had sat down and had a long talk. The outcome was that enough was enough; Sam wanted to move in with Sarah down in Lebanon, and whilst he and Dean would keep the Bunker going as a resource for the hunter community, their days of tackling the supernatural head-on were done. Cas sat there just nodding in agreement, and it was only after his brother had left, and he and Cas were drinking hot chocolate at the kitchen table, that it hit Dean.

He could have lost Cas.

Yeah, the angel had died for him countless times in the past, but he had always come back. But seeing Metadouche standing over his friend's wounded form was an image that would haunt Dean to the end of his days, even if he knew that Cas had volunteered to act as 'bait'. And now, it was all over. Hannah (with more than a little help from Charlie, Dean suspected) had been running Heaven efficiently up to the final battle, and all his friend would need to do now was check in occasionally with her. 

“What is wrong?” Cas asked, breaking into his thoughts. 

Dean blushed.

“Just wondering what your plans are”, he muttered, not looking at the angel. “I mean, they'd have you back upstairs now, I s'pose.”

Cas smiled. And that was the precise moment when Dean Winchester realized that stopping hunting might not be an end to his troubles. Because when he saw that cute little face light up, with those crinkling eyes and that gummy smile, he just wanted to take Cas to his room and pound him into his memory foam until it remembered the angel as well as him.

“I rather prefer it the other way round”, Cas said with a smile.

Dean looked at him in confusion.

“Huh?” he managed.

Cas reached over and ran his hand along the hunter's jaw. Dean may or may not have leaned into the caress, and there was a strong probability that the longing keen that echoed round the room did not originate from the angel.

“I prefer to top”, Cas said with a smile. “Unless you would rather rest after....”

The rest of his sentence was lost as Dean yanked him out of his seat and dragged him forcibly along the corridor. Cas went more than willingly.

+~+~+ 

Dean didn't remember much of the next few days, or for that matter most of that November. He would have smiled at the thought that this was the same angel who had once run with him from a brothel, but the act of moving his facial muscles was just too much. Cas had seemed determined to make up for his billions of sex-less years just existing, and Dean, great guy that he was, graciously allowed him to do just that. Even if he had to be careful when sitting down over those few days. 

Or walking. 

Or breathing too sharply.

+~+~+

Sam moved into Sarah's house earlier than planned.

+~+~+

It was November 30th, and after a night's rest - Cas had told him his body needed it, and reluctantly the hunter had been forced to agree – Dean had decided that he and the angel were going Christmas shopping. Cas looked as bemused as ever at the nightmare that was the local megastore, but that small smile made Dean light up inside, and think that, with any luck, he and Cas might make this a Christmas to remember. If Dean's body was up to it, that was!

Though the hunter's eyebrows rose when Cas insisted on going into the adult store alone, and then refused to let him see the purchases in his very large brown paper bag. Dean may or may not have given a little yip of happiness that pulled a smile out of the scruffy angel, but he was not totally whipped.

He was sure that Cas was behind the fact that, seconds later, he passed a travel agent's and saw a poster advertising cruises down 'De Nile'.

+~+~+

“I have been giving some thought as to your Christmas present”, Cas said over dinner that evening. 

Dean looked up in surprise, then sighed. The grub had somehow got ketchup all down his front again. He fetched a cloth to wipe it up, earning himself a grateful smile that did happy things to his insides, even if it made what remained of his manliness weep. 

“You don't have to give me anything, Cas”, the hunter grinned. “Though if you wannna start working through what you got from the shop earlier.....”

“”I already have something planned, and it includes that”, the angel said. “I will set it up in our room some time tomorrow.”

Dean felt a warm sensation at that. 'Our room'. Technically Cas had his own room adjoining the hunter's, though it was no longer used, and the bed had not even been made up. Cas now spent every night in Dean's bed, on top of or under the hunter. Except for one particularly athletic encounter which had led to Dean being fucked whilst pinned to all six surfaces – including the goddam ceiling! - by Cas' wings. The memory of that made the hunter's smile widen even further.

“What is it?” he asked, dragging his reluctant mind out of the gutter.

“An Advent Calendar”, Cas said. “A most intriguing human custom. Rather than one large present, the recipient gets twenty-five small presents, one each day running up to Christmas.”

“Cool”, Dean grinned, secretly wondering if it would be chocolates. Or even pie? A miniature pie Advent calendar. His mouth watered at the prospect.

“Gonna give me something to keep me going till then?” Dean asked lasciviously. 

The angel gave him a look. It was the sort of look that promised extremely good things for a certain hunter, whose pants were suddenly very tight......

“Tomorrow”, Cas promised him. “It will be worth the wait, trust me Dean!”

Dean did not whine. It was a cough that came out wrong.

+~+~+

Yes it was!


	2. December 1st

**Summary for the Chapter:**

> Is this a dagger I see before me?

Cas left the kitchen immediately after dinner, telling Dean he could open the first door on the calendar at eight o'clock, no sooner – oh, and it was locked by the angel's grace until that hour. Meanie!

Dean went to his room at five minutes to, and was more than a little surprised. The 'calendar' turned out to be the size of a giant bookcase, six foot high and close on twenty across, split into a set of five by five rectangular boxes. The front was a montage of Christmas scenes, and he had to look for some time to find door 1, which was slightly left of center. Then he had to watch the bedroom clock work its way painfully slowly to eight o'clock, before tentatively opening the door.

He stared in surprise. Inside was one of Cas' throwing-daggers, a small thing about three inches long and infused with a tiny amount of the angel's grace. It looked ineffectual, but Dean knew that once embedded in a target, the angel could connect with the grace inside it to cause an explosion that would take out the victim and anyone or anything close by. He was still wondering at such a thing when the connecting door to Cas' room slowly swung open.....

+~+~+

Dean Winchester had entered many rooms in his lifetime, and faced all sorts of surprises therein. But it was probably safe to say that few, if any, matched his reaction to what he found in his lover's room just then. Cas stood in the center of the room in full warrior kit, his metal armor shining almost brightly enough to distract Dean from the huge black wings pulsing gently behind him.

Almost.

Dean could have sworn he felt dizzy, as every drop of blood in his body tried to simultaneously make for his lower brain. Cas smiled at him.

“You have done so much, Dean”, he said gently. “For humanity. For me. It is time you had a reward.”

What were those things Dean had been quite capable of earlier that day? Oh yeah. Words. Damned if he could manage any of the tricky fuckers now, though.

“I want you to help me out of my armor”, Cas smiled. “All of it, Dean. When you're ready.”

Somehow there was just enough blood left in his legs for Dean to stumble forwards, and fumble uselessly with the breastplate that shone in the dim light from Cas' bedside lamp. Somehow he managed to get it loose, and it slipped off the angel, passing easily through the ethereal black wings. Wings that were only that color because.....

“Because I loved you from the moment I gripped you tight, and raised you from perdition, Dean”, Cas said, most unfairly cutting into Dean's self-deprecation. “And they tell every other being I meet that I am Dean Winchester's angel, and no-one else's.”

Dean managed a strangled noise that would have made more sense coming from a walrus mating colony. He fumbled with Cas' jerkin, eventually managing to get it off to reveal that perfect toned body – why the hell hadn't Jimmy Novak gone into modeling rather than selling radio time? - and ran his hands over Cas' chest, sighing happily.

“Finish the job!” the angel growled.

Oh yeah. Multidimensional wavelength of celestial intent, who might start smiting Dean if he didn't get a move-on. The hunter undid the leather belt and pulled down the battle-skirt.....

Holy fuck! Cas went commando!

Dean didn't even have to think about it. Some gut instinct led him to take Cas' semi-erect cock in his mouth, almost choking himself in the process. He felt rather than saw the angel stiffen, and the thick rod hardened in his mouth as Cas let out a guttural moan. Dean eased off, and began to lick along the thick underside of the cock, making the angel groan again, and the hunter had a front-row seat as Cas exploded, his come splattering from his chest to several feet across the floor.

“Awesome!” Dean muttered, quite proud he had found his voice again. Cas panted for some time before answering.

“You have your voice back”, he said with a smirk. “Let's see if I can fuck you hoarse by the end of the evening!”

And this was just Day One! Hell, Dean might not survive until Christmas. But Cas could always bring him back to life again, and at least he would always die happy.


	3. December 2nd

**Summary for the Chapter:**

> Dean gets to play barista.

Dean was not nervous as he went to his room that evening. No sirree, he was not. He was only shaking because the room was cold.

He was puzzled, perhaps, when he located and opened Door 2 to reveal an empty unused coffee cup. He picked it up, and sure enough, the door into Cas' room opened slowly as he did so. Swallowing nervously, the hunter went through.

He noticed three things straight away. First, this was some sort of coffee place, and Cas was stood to the side of the counter. Second, said angel was wearing a barista apron and sod all else. And third, judging from the sudden coolness in Dean's nether regions, he was wearing exactly the same.

“I think you promised me a coffee, Dean”, the angel grinned, gesturing to the empty cup.

Dean nodded – he'd already figured that words were not going to feature strongly in these encounters, at least from him – and made his way behind the counter to the coffee machine. It looked simple enough, a single lever which, when pulled, would release the coffee into the cup below. He had just got the lever down when he felt Cas move in close behind him, and yup, the bastard had moved his apron to the side. Which meant that Little Cas was nestling right up against Dean's crack. Dean moaned, but managed not to push back – until Cas started rubbing his cock up and down. Now that was just unfair!

A second moan elicited a slight nibble at his neck, and Dean stared down blearily at the cup. Barely a quarter full; damned angel must have set the machine on slow. And now Cas' cock head was pushing against his entrance. Dean let out something that an uncharitable observer may have described as a whine, and arched his back.

“Eager”, Cas chuckled darkly, rubbing one hand along Dean's bare arm. “Good boy. You're so beautiful like this, Dean.”

Trust the sneaky angel to break out the compliments when Dean wasn't exactly in a position to argue. The not-whine became a moan of happiness as Cas pushed slowly in, and Dean felt himself getting fuller and fuller....

And that was the precise moment that, with no warning, Cas' other hand suddenly ran the length of Dean's hardening cock. Dean yelped in shock and came violently, his flailing arms banishing the cup and its contents to some distant corner of the room, he knew not (or frankly cared not) where. His body shuddered through one almighty orgasm, until it finally subsided into Cas' strong arms.

“Honestly!” Cas said in what was clearly mock disapproval. “You've ruined my coffee, Dean. Now you'll have to make me another one.”

In what remained of Dean's upper brain, he thought, hell yeah!

+~+~+

It took five goes before Cas got his coffee, and he was able to enjoy it in the bed he teleported them both to, cuddling with what remained of his resident hunter. Who would never be able to go into a coffee place again without smiling in a way that those closest to him knew full well not to ask about.


	4. December 3rd

**Summary for the Chapter:**

> Take a letter, Mr. Winchester!

Door 3 lay just above Door 25, which was in the exact center of the boxes. Dean was nervous when he opened it, and more than a little surprised to find a notepad and pencil inside. Picking the both up, he went through the now open door into Cas room to whatever awaited him there.

This was some sort of office, with way too much glass. Cas dressed in a suit and tie, sat in one of those ridiculous huge black padded chairs which made him look smaller than ever, though the huge cock he was handling did set that off a bit. Dean may or may not have drooled just a bit (a lot).

“Ah, Mr. Winchester”, Cas said in his usual deep rumble. “Take a seat, then I have some dictation for you.”

Certainly the dick, never mind the tation, Dean thought wryly as he all but ran over to straddle Cas' chair. The angel must have used his grace on him, because he lowered himself down onto that monster with no effort, though he certainly felt full once he was (very comfortably) seated. 

“Dear Sir”, Cas began calmly. “In response to your recent letter.....”

Oh yeah, the writing. Dean scrambled to get his notepad, but hadn't even got the first word down before Cas twitched his dick inside of him, deliberately targeting his prostate. Dean moaned in ecstasy. 

“Pay attention, Mr. Winchester”, Cas said, and damn, the bastard had somehow gotten a cock-ring around Dean's already swollen cock. Bloody fast mover! Dean whimpered, but managed to write something on the paper, though whether it made any sense or not he didn't know. Or care, for that matter.

“Pursuant to our earlier discussions....” Cas rumbled on, and now the bastard was twitching inside of him and fondling his balls at the same time. Dean's eyes watered, and he stared out of the fake glass windows sightlessly, tears forming in his eyes. Cas was gonna kill him!

“Therefore, to conclude, I am sure you will agree we should come together on this”, the angel said, thrusting extra hard on the 'together'. Dean could feel the cock-ring strain, but the damn thing held. Cas meanwhile was unbuttoning Dean's shirt and running his hands over his chest, which was Not Helping.

“Yours faithfully, et cetera”, Cas finished off. “That's it for the first letter.”

Somehow that made it through to what remained of Dean's upper brain.

“First?” he squeaked.

“Of course”, Cas said. “I have six more for you, Mr. Winchester.”

And with that he thrust again. Either the cock ring broke or Cas must have mojo'ed it away, for Dean fairly blew, his come flying up between them as he arched his back in ecstasy. Cas continued to play with his chest until he finally stopped, panting hard.

“Now”, Cas said. “Letter number two. This one is rather.... longer.”

He thrust in again, making the hunter yelp. 

+~+~+

Dean was never hitting on a secretary again!


	5. December 4th

**Summary for the Chapter:**

> 6 or 12?

The lower left-hand side of the units was where Dean eventually found Door 4, and inside was.... a brown paper bag? An empty brown paper bag?

Weird.

The door into what should have been Cas' room took him instead into what looked like a fitting-room of some sort, entering opposite the closed blue curtain. On the cheap IKEA stool there was a folded pair of black lace silk panties – hot damn! – and standing prominently on top of them, a rather large butt-plug. Dean's eyebrows shot up, but he quickly shucked off his clothes and, after working himself open, got the plug inside. The panties fitted him perfectly, and he pulled back the curtain, bracing himself for whatever was on the other side (hopefully one very horny angel).

Cas was there, stood behind a counter in what was undeniably a sex-shop. He smirked at Dean as the hunter sauntered up towards him, wincing only slightly as the large plug brushed his insides. 

“The R6 model is one of our best-sellers”, the angel grinned, placing what looked like a small TV remote on top of the counter. “I presume sir would like to try it?”

“I already have”, Dean said, puzzled.

Cas smirked, and pressed a button on the remote. The next moment, the plug juddered to life, and Dean actually jumped into the air at the shock, shrieking in surprise.

“Hmm, I can see from your choice of lingerie that that definitely had the desired reaction”, Cas grinned, leaning over the counter to rub his hand against the front of the now wet panties barely encasing Dean's suddenly very hard cock. “Perhaps a cock-ring would be advisable before sir proceeds any further?”

“Further?” Dean squeaked. 

Cas grinned, and pressed the remote again. This time Dean positively screamed, shaking as he came violently. How he remained upright was a mystery. Cas grinned, and mojo'ed him clean once he'd stopped.

“That was setting number two”, the angel said, and Dean began to have a very bad feeling about this. “As the name suggests, this particular model has six settings, each more intense than the last.”

Dean barely heard him, concentrating as he was on trying to get his heart-rate back to normal. Once his breathing had steadied, he managed a weak “six settings?”

“Six settings”, Cas confirmed. “Perhaps sir would care to try the remaining ones whilst lying down. We have a memory foam mattress out the back.”

Dean nodded vigorously, trying to remember how to put one leg in front of the other. He had even managed a couple of steps before Cas spoke again.

“Unless”, he growled, “sir would prefer to try the R12?”

Dean could only hope that he would recover in time for the next day's activities. And yeah, he was definitely trying the R12!


	6. December 5th

**Summary for the Chapter:**

> Crime does pay - sometimes.

Dean stared at the contents of Box 5 with some trepidation, if not fear. Handcuffs? 

Kinky time! With a supernatural being who could smite him without breaking a sweat. Okay.....

Dean walked a little more cautiously through the open door this time, but was still unprepared for what awaited him on the other side. A dull gray room with a single table, by which the angel was standing in.... hell yeah, the trench-coat (which Dean may, just possibly, have had a thing for). 

Dean suddenly found two things. First, his feet had apparently locked themselves to the floor, and second, his arms had not only shot above his head, but were cuffed to each other and a chain hanging down from the ceiling that, he was sure, hadn't been there when he had entered the room. Fuck!

Cas sauntered round to his side of the table, and smirked.

“Need to find out of you have any dangerous weapons on you, Winchester”, he growled.

“Only the one in my pants!” Dean quipped back, quietly proud that, for once, he could actually manage those things called words.

At least until Cas ripped his pants off of him with a single pull, throwing them to a corner of the room, and pulled Dean's plaid shirt open. Then he knelt down and began to run his hands up from Dean's calves, giving the hunter an instant (and painful) erection that made him yelp.

“You don't seem to be hiding anything”, Cas mused as he passed the backs of the hunter's knees, but with those bowed legs, I can't be sure. I guess I have to be thorough, eh?”

And with that Dean felt a finger pressing at his entrance and – oh, now that was just unfair! Cas was using his grace to open Dean up for him, and that did things to the hunter that made an orgasm almost inevitable. Dean whined.

“So pretty”, Cas purred. “But the shirt – plaid doesn't really suit a hardened criminal like you, Winchester.”

Definitely hardened, Dean thought wryly as the shirt was ripped from him (he'd have to get Cas to repair it later; it was one of his favorites). Then he felt something else draping over his shoulders, and his eyes widened. 

Cas had put his trench-coat on Dean.

The shock of feeling such a familiar garment was so much that Dean didn't even notice the angel had slipped behind him – until Cas went straight for his prostate. Then he noticed, coming violently as the open flaps of the coat fluttered at the edges of what remained of his vision.

“Nothing in there”, Cas said, sounding disappointed. “Now, I think an oral search as well.....”

Dean's eyes widened. Oh fuck!


	7. December 6th

**Summary for the Chapter:**

> Ho ho hose!

Door 6, on the bottom row of the boxes, contained a small magnifying glass. Dean picked it up, examined it for a few moments, then shrugged and walked through the door into....

Cas' room.

All right, that was perhaps a bit disappointing. Nothing seemed to be out of place, except that there was a folded piece of paper on the bedside table. Dean unfolded it, but the writing was minuscule, so he used the glass.

“Fire?” he muttered.

His voice came out uncommonly loud in the small room. As if by magic, a pole appeared next to the bed on which he was sitting. And sliding down it was one one tousle-headed firefighter, looking at Dean in a way which stated quite clearly that someone was in for a most interesting night.

“Not another idiot with a false alarm!” Cas said in a put-upon manner. “Honestly, I get all ready to serve the public, and for nothing.”

Dean's lower lip quivered, as the angel began to strip off the uniform. Cas was wearing that sexy blue top that was a bit tight and showed off his muscles perfectly, and down below..... holy cow, he was going commando again! Wearing just the tight top, the angel stalked to the end of the bed.

“Firefighters get very stressed serving the public”, he growled, and as usual the Voice was making Dean even harder. “”They need plenty of rest and relaxation in their downtime, you know.”

“Yeah?” Dean squeaked. 

“Oh yeah”, Cas growled. “And what better way to relax than to come home to a hot man, who's already on fire. In fact, I think I'd better help put that fire out, Dean. I have just the instrument to do it with.”

Dean prayed silently that Cas didn't mean the hose.

He didn't. But he did thrown Dean face down onto the bed, and slowly insert himself into him, making happy growling noises all the while that had the hunter leaking all over the bed. Dean felt his orgasm approaching, only for Cas to suddenly flip them over.

“My own personal hose!” Cas whispered from behind.

And Dean erupted, his come flying all over the room as Cas pumped into him from behind. As his remaining brain cells packed up for the evening, his last but one coherent thought was that Cas must have been somehow recharging him, because no-one could come for that long.....

His last thought, before he passed out, was that Cas was kissing him and whispering how much he loved him. He was one lucky sonovabitch!


	8. December 7th

**Summary for the Chapter:**

> Dean in a skirt - sort of.

There were few things more annoying to Dean than the feeling he had seen something some place else, and the small metal badge behind Door 7 with the letters 'SPQR' on it was irritatingly familiar. He just couldn't place where he'd seen one like it before. Sighing, he walked through the open door to Cas' room.

He felt the cool air immediately, which was hardly surprising as he now seemed to be wearing some sort of leather skirt, sandals, and not much else. Cas was sat on a long, low couch-thing at the end of the room, which itself was painted with old-style pictures.

“Senatus Populusque Romanus”, Cas said quietly. “The Senate and the People of Rome. The letters borne by the legions of the Empire, whose idea of amusement was to watch grown men kill each other in a crowded stadium.”

Oh yeah, that was where he'd seen it before. The two of them had done a Roman-style LARP with Charlie some time back, and Cas had been wearing the same sort of bed-sheet – toga, Dean recalled – he was now. A toga that now did precisely nothing to conceal that Cas was most definitely aroused by the sight of the gladiator who had just entered the room.

“Some think your name may come from the Latin 'decanus', meaning 'of ten'”, Cas said, beckoning Dean across the room. “A decurion was a leader of ten men, as a centurion was of a hundred. And rich, powerful Roman leaders often had their own personal gladiators for... private entertainment.”

Somehow Dean had crossed the room without telling his feet to move. Cas slipped gracefully to the mosaic floor, and began to rub his hands up Dean's legs. The hunter growled his approval.

“Pteruges”, Cas muttered from where his head was now up inside Dean's skirt. Dean would have asked the obvious question, but at that precise moment Cas tongued the tip of Dean's now very erect cock, and instead the hunter just moaned.

“It is the word for the skirt you are wearing”, Cas said, and Dean was surprised he could hear him, his senses all but shutting down under the assault. “Manly Decanus, wearing a skirt. Only you could pull this off, Dean.”

And with that Dean felt the angel's fingers teasing at his balls, and he came with a shout. Cas jerked him off through it, and continued to rub his cock even when he was done. To Dean's amazement (and alarm), it immediately started to become hard again.

“The straps of the pteruges would be decorated with the mark of the gladiator's patron, or with his greatest achievements”, Cas said, and holy cow, now he was using his tongue in between sentences. Dean's eyes watered. “I think a special one tonight to mark a whole number of successive orgasms. I wonder if we can match your name, and make it ten?”

With what remained of his brain, Dean's opinion of ancient history was undergoing a rapid improvement.

+~+~+

Yeah, he kept the sk... pteruges. So?


	9. December 8th

**Summary for the Chapter:**

> Yee-hie!

The eighth door, in the top middle, was decorated with a Santa hat. This proved appropriate, because inside was a stetson. Dean looked at in in confusion, then put it on and walked through the open door....

Oh fuck!

The hunter found himself suddenly kneeling down on the bed, his ankles and knees tied to the four corners and his wrists tightly bound behind him, albeit with mercifully soft ropes. He was trussed up tighter than a Thanksgiving turkey, but was still wearing the hat. Just nothing else.

He heard the clink of spurs from somewhere, and looked up. Cas was stood in the doorway, wearing cowboy boots and a hat.

The hat was not on his head. Dean whimpered, especially when the hat began to rise.

“Looks like we're gonna be able to prove the truth of that old saying, Dean”, Cas smirked, walking round to straddle the hunter on the bed. 

“Wha.... what old saying?” Dean yelped, as Cas went straight for two fingers. Damned angel was over-eager tonight.

“Save a horse, ride a cowboy”, Cas said, and Dean could hear the smirk even if he couldn't see it. Then Cas pressed down onto his prostate, and further conversation became somewhat difficult.

“Such a good ride”, Cas muttered, and Dean's eyes watered as the angel pushed into him. And to think he had once described angels as 'junkless'. Hah!

Cas gave him a moment to accommodate himself to being filled, then thrust forward. Dean realized that the mirror on the wall opposite gave him a view of his angel, who was now waving his own stetson in the air. Then Cas caught his prostate again, and Dean's vision blurred.

“Ride 'em, cowboy!” Cas all but yelled. The hunter, unable to move under all the binds, could only clench his muscles against the invading cock, but that was enough to make Cas come with another shout, until he collapsed onto Dean's body. The hunter panted under the sudden weight.

“Cas!” he protested.

“Time for another ride”, Cas whispered into his ear.

Oh yeah. Angel. Zero refractory time. Dean's poor butt!

The hunter was gonna need extra cushions the following day.


	10. December 9th

**Summary for the Chapter:**

> There is pie.

Door 9 was on the bottom-left of the unit, and Dean opened it to a surprise – a pie box from his favorite local bakery.

The second surprise was that it was an empty pie-box from his favorite local bakery. Figured! Picking up the empty box – hey, you never knew your luck! - he walked through the open door.

Holy cow, it was his favorite local bakery! Or at least a pretty damned good copy he slowly realized; everything beyond the table in front of him was slightly blurry and out of focus. And sat at that table was one scruffy angel, eating what was most obviously the former contents of the box Dean was holding.

It be nice to say that Dean Winchester made it to the table without drooling excessively, but then again, it would also be inherently untrue. He scooted in opposite his angel and looked pleadingly across the red-and-white checkered tablecloth. 

“I hope you remember that Sam put you on a diet, Dean”, Cas said, nibbling at the perfect crust on his slice. “Especially after you found your jeans no longer fitted.”

“They must've shrunk in the wash!” Dean said defensively. “Cas! Pie?”

It was blatantly unfair that, whilst his angel and his brother both had perfected the puppy-dog look that got them whatever they wanted, on Dean it always ended up with him looking mildly constipated. Cas was clearly unaffected his his efforts, and reached for the cream.

Dean watched as the angel ate his latest slice, and suddenly had an idea. Carefully reaching across the table, he pulled the angel into a kiss, and hallelujah! Cas tasted of pie and cream. Even better than usual!

The angel grinned at his obviousness.

“Are you really going to try to eat my pie out of my mouth, Dean?” he smirked. “Because there are at least four more slices here. Unless you want to take it to go?”

“Hell, yeah!” Dean grinned.

Which was possibly a mistake, because the diner promptly disappeared, and Cas was lying naked on the bed in his room, the latest slice of pie balanced on his perfect chest. 

Dean was gonna have an aneurysm. Especially as, to reach the pie, he had to get past Cas' very erect cock.

It was gonna be a long night.

+~+~+

It turned out that, yes, you could pass out when eating pie. At least when doing it off of a horny angel!


	11. December 10th

**Summary for the Chapter:**

> Another history lesson, and it's all Greek to Dean.

Door 10, just below Door 25 in the center, revealed a scrolled-up piece of paper. Unraveling it, Dean read the following:

ἐραστής 

Some weird foreign language, which Sammy would doubtless be able to translate at once. And Dean quickly put thoughts of his brother out of his head before going through the open door. So not the time!

He found himself in a warm room, which seemed to be mostly white stone and a few wall-paintings. He was however a bit more concerned about two other things, the first of which was Cas wearing some a white tunic with a short (very short) skirt, standing there waiting for him.

The second thing was that Dean was butt naked. Okay, so no messing about, then.

“The word on the scroll is 'erastes'”, Cas explained. “It is Greek, referring to an adult male who takes a younger lover, the eromenos.”

“Sounds a bit illegal”, Dean hedged, walking slowly towards his angel.

“Actually, the eromenos got to choose their lover, although of course they were often pressured by their parents to choose well”, Cas told him. “And often the relationship would continue even after it was formally over, when the erastes would give his eromenos a parting gift to set him up in adulthood.”

He reached down, and placed a crown of leaves on Dean's head. The hunter smiled.

“Well, you're certainly the older one of us”, he quipped. “And what if I don't want to be let go?”

Somehow Cas managed to pull him inside the sheet he was wearing, and yup, the sheet was all Cas was wearing. Dean sighed happily as their cocks rubbed together.

“There is a modern saying, I believe”, Cas whispered into his ear. “If you love something, set it free. If it comes back to you, it is yours. If it does not, then it never was.”

Dean let out a keening noise as Cas rubbed his cock towards a full erection. Damned sneaky angel was using his grace as well, he was sure.

“Don't wanna be let go!” he managed.

Cas chuckled.

“Be assured that I have no intention of ever letting you go, Dean Winchester”, he said quietly.

And with that he did that thing with Dean's balls that had the hunter coming violently, collapsing into the angel whom, he knew, would always be there to catch him. 

+~+~+

All right, so Dean now liked Roman and Greek history!


	12. December 11th

**Summary for the Chapter:**

> There is an examination.

The eleventh door proved hard to find, center left behind a reindeer that reminded Dean of his moose of a brother who, it seemed, kept intruding into Dean's mind at the worst times lately. Inside, Dean found.... a TV scheduling magazine?

He was browsing said magazine when he walked through the door, so he was caught off guard when he found himself in what was most obviously a doctor's surgery. Oh yeah! Doctor Sexy!

And as that thought was well on the way to making Dean hard, Cas walked through the other door wearing a doctor's coat which, from the tenting at the front, was all he was wearing. And yup, cowboy boots. This was some sort of test to see if Dean could survive without passing out.

(He was probably gonna fail). 

“Mr. Winchester”, Cas smirked. “Thank you for coming in for your regular prostate check-up. Clothes off and onto the couch, if you please.”

Dean smirked back, and began a slow striptease which, judging from the increasing tent in the front of Cas' regretfully closed doctor's uniform, was definitely having an effect. He hoisted himself up onto the couch and waited.

“I remembered that you quite liked the honey-flavored lubricant I used last time”, Cas said, and hot damn if the bastard hadn't shucked his coat and was sauntering round to his work station, making the hunter moan in anticipation. “But I purchased something a little different this time.”

He must have moved faster than Dean had expected, because suddenly two fingers were opening him up, and he could feel the lube rapidly coating his insides. It smelled like....

“Pie, Cas?” Dean asked incredulously. 

“Cherry”, Cas informed him. “It helps to take you mind off things, so you are less alarmed when I do... this!”

And suddenly there were two fingers pressing down hard on Dean's unsuspecting prostate. The hunter yelped in shock and orgasmed without warning, his cries becoming a long drawn-out moan of pleasure as Cas continued to massage his prostate with the wonderful lube.

“Definitely a positive reaction”, Cas whispered. “But I think we need to do a more thorough examination today, Mr. Winchester. Do not worry, though. The... instrument that I shall be using will also be coated with the same lubricant.”

Fucked by an angelic cock coated with cherry-pie-flavored lubricant, Dean thought with a grin. Maybe, just maybe, there were one or two small upsides in being a hunter.

Then Cas eased home in one swift movement, and Dean thought no more.


	13. December 12th

**Summary for the Chapter:**

> Dean doesn't hate libraries any more.

**Notes for the Chapter:**

> Though I'd corrected my mis-posting yesterday, but apparently not. Things seem to be back in order now.

A book. On mathematical equations. 

Dean stared at the contents of Door 12, perplexed, then shrugged, picked it up and walked through the door into.....

A library. And there, sat behind a glass desk, was Cas, dressed as a sexy librarian. Complete with that damnably unfair waistcoat which, the angel knew full well, did Things to Dean.

All right, the fact that Cas was wearing the Perfect Sexy Librarian Outfit™ only from the waist up, and that the glass desk gave Dean a magnificent view of Not-So-Little Cas may just possibly have been a very small contributing factor to the hunter's sudden erection. His angel knew him so well.

Cas looked up as he approached, and took the book from him, examining it carefully. A frown creased his gorgeous features.

“This book is late back”, he growled. “You have been warned about this before, Mr. Winchester.”

Dean just nodded. Back to no words again, it seemed.

“I suppose that I might be prevailed upon to overlook this latest in a long line of offenses”, Cas said, sounding majorly put upon. “If you can get me off before I finish this particular book, that is.”

The hunter nodded frantically, and quickly removed his clothes before scooting in behind the desk and taking Cas' cock in his mouth. It was already half-hard, and Dean had learned several tricks to get his angel off, all of which he knew were greatly appreciated, at least judging from the heavy breathing he could hear above him. But Cas had clearly been putting in practice, and managed to hold off.

“Last page”, the angel said, his voice clearly strained.

Dean thought fast, and reached behind Cas' balls to tickle the soft skin there. At the same time he sent a mental image of the angel having a wonderful orgasm, and to his relief it worked, Cas coming down his throat with what was close to a snarl. Dean swallowed it all, allowing himself a slight smirk in the process.

“Very good”, Cas praised. “You achieved your target before I had finished Volume One. I am now going to start Volume Two.”

Dean tensed. What?

Only five, he heard Cas think in his head. Then I am going to take you behind the hardbacks.

The hunter's eyes watered. Hell, his school library had never been so..... educational!


	14. December 13th

**Summary for the Chapter:**

> To boldly go....

Door 13 was on the top right of the boxes, and Dean opened it to find.... an aerosol containing just water spray? Huh? 

He walked through the open door into whatever awaited him, and found himself in pitch blackness. Which was one surprise. The other was that for some reason he couldn't stop, and walked if not floated straight into the opposite wall with an 'oof!'

“Hullo, Dean.”

Cas. Somewhere in this room.

Dean instinctively looked down, and found that he was wearing a gold command Star Trek top from the original series, along with black boots. Everything except the pants. Which probably meant that this was LARPing, which in turn meant that Cas was somewhere in the room wearing the blue science officer's top and, similarly, no pants. 

Dean may or may not have drooled. A lot.

“You have to catch me first”, came a teasing voice from his left. 

Dean was about to walk over to investigate when he realized. Zero gravity. He'd only end up splatting into another wall, and perhaps even be too bruised for sex – well, unlikely, but....

Aha! The water spray. He pointed it behind him, and sure enough, it propelled him towards where the voice had come. He caught a glimpse of Cas' naked form before there was a second hiss, and the angel moved easily out of his way. Dean whined.

“Close!” Cas called teasingly.

Dean found himself getting more and more worked up, as every time he used the spray to close in on the teasing angel, Cas eased himself out of his way. Then, just as he feared his spray was running out, he heard the familiar creak of the angel's bed, which he knew was on the far side of the room. Right!

Dean propelled himself over to the bed, easing himself along it and finding... nothing. What on earth....?

He heard the tell-tale hiss from above and behind him a fraction of a second too late. Cas must have used his mojo, because there was no way Dean Winchester could normally take being impaled by that monster. The hunter yelped in a mixture of surprise and shock, as Cas' arm pulled him closer.

“Now”, the angel whispered in his ear, “hang on for the ride!”

+~+~+

It is, perhaps surprisingly, possible for a human to experience an orgasm whilst doing a complete 360 roll in zero gravity. But not, it turned out, to remain conscious afterwards, even if he does pass out with a smile a mile wide on his face.


	15. December 14th

**Summary for the Chapter:**

> Not every sort of runway is bad......

Center-bottom was where Dean found Door 14, and again, the contents were puzzling. It looked like a small fan, except that the four wings were each numbered, one through four. The hunter stared at it curiously, but reasoned correctly enough that enlightenment would soon follow. He strolled through the door. 

This looked like some sort of small auditorium, except that there was a raised runway at the front ending in a round area. Dean was still trying to work it out when he heard Cas' voice:

“And number one, our model displays the ultimate in silken luxury, black male panties.”

And sure enough, there was Cas standing there, wearing nothing except a pair of almost transparent black panties, which were doing nothing to hide the impressive bulge beneath. Dean drew a ragged breath.

“Note the generous area at the front, and that the sides can be personalized with your lover's name if so desired”, came Cas' sonorous voice. “Or perhaps you might prefer number two, the short kilt.”

In the time that it took Dean to blink, Cas had changed into a short tartan kilt. A bit too short, given Cas' length. Dean was gonna have an aneurysm!

“Very useful if your lover wishes to exert a hands-on approach at short notice”, Cas' voice came, and damn it, Dean could hear the smirk. “And easy to remove, even in the back of a classic car. Unless sir's preference is for number three?”

Dean instinctively tried to keep his eyes open, but he was forced to blink, and..... hot damn! Cas was wearing a skin-tight leotard top, that hugged every muscle from his shoulders down to... there! 

Dean was definitely drooling. No two ways about it.

“Of course, a popular favorite is number four”, the voice came again, and Dean looked around for something to grab for support. In doing so he momentarily took his eyes off of Cas, which was a mistake because....

A black G-string! Cas was wearing a black G-string! Held up only by the Hips of Doom™ and a seriously impressive erection.

Dean came with a shout, his vision blacking out for a moment (which he regretted), but when he came to, Cas was still standing on the circular area, smirking more than slightly. Dean fumbled for the fan-thing, and quickly held up the '4'. 

“I'll throw in the others for later”, the angel grinned, sauntering off the stage with far too much delicious, lickable skin. “After we've finished with the G-string, that is.”

Hot damn!


	16. December 15th

**Summary for the Chapter:**

> Ball games.

Door 15 was just to the right of the center door. Dean opened it, and yet again, he was more than a little surprised at the contents. And being Dean Winchester, he immediately thought.... no, Cas wouldn't.....would he?

It was a football. Fully inflated, since you ask.

It was no real surprise for Dean to go through the door and find that none of his clothes had come with him. By the heat and noises, he was in some sort of communal shower room, and.... holy mother of God, Cas was standing next to a shower-head and peeling himself out of a football uniform. Dean would never be able to hear the phrase 'tight-end' in future without smiling.

“Hey, it's the rookie!” Cas grinned, finishing his strip-tease and moving to stand under the shower-head. “Well, come on Winchester. The team's star player needs a good wash-down, you know.”

Dean managed a noise which, if one was feeling charitable, might have suited either a stroppy kindergartener or a particularly well-oiled drunk, and almost fell over his feet as he hurried forward. He reached to get the shower gel, and began to rub it into the angel's broad shoulders, only to pause and sniff at it curiously.

Okay, so they did apple-pie scented shower gel nowadays. God Bless America!

Dean was trying, he really was, but the pleased little sighs and moans that the angel kept putting out was making it hard. In both senses. 

“No coming before the star player”, Cas informed him sharply. “Or do you need the cock-ring again, Dean?”

The hunter shook his head, and continued his way down to Cas' Hips of Doom™, before deciding to try to turn the tables on the teasing angel. Brushing only lightly against that perfect angelic ass, he moved down to Cas' calves, and began to slowly work his way back up. 

Cas continued to moan happily, and Dean smirked. Without warning, he suddenly reached round and did that thing with the angel's balls that he knew he loved. Cas let out a mighty roar and came violently, Dean continuing to massage him through his orgasm until he was done.

“Definitely worthy of the team”, the angel panted eventually. “Provided, of course, your performance in washing my front is equally satisfactory.”

Dean grinned, and moved round to start.


	17. December 16th

**Summary for the Chapter:**

> Dean gets a new belt.

There was a small, old-fashioned looking metal key on a chain behind the most top-left of the twenty-five doors. Oddly, it disappeared as soon as the hunter reached for it. Puzzled, Dean waited to see if it would reappear, but when it didn't, he shut the door and went into Cas' room. 

Except he found himself in some sort of medieval castle bedchamber. Which would have been great – Dean loved LARPing, and the bed was an added bonus – but he was slightly more concerned that he was suddenly naked except for some strange leather contraption wrapped around his waist....

“Hullo, Dean.”

Damned sexy angel, materializing from nowhere onto the bed, where he was enjoying a platter of fruit and other way-too-healthy food. Dean looked at him in confusion.

“The item you are wearing is called a chastity belt”, Cas smirked, “though in your case.... well.....”

“Hey!” Though to be fair, the angel had a point.

“Medieval barons would often go off fighting in distant lands, and they wanted to be sure that their loved ones would remain faithful to them”, Cas said, twirling what Dean recognized as the vanished key. “The chastity belt ensured that they and they alone had access to their mate's favors. And to the mate, of course, it was a permanent reminder of who owned them.”

In a blink, Dean found himself kneeling on all fours, his butt facing the angel who was clearly using the key to unlock the damned belt. Then Cas inserted a single finger, and Dean's upper brain promptly waved a white flag. Except that the damned angel was deliberately ignoring Dean's prostate, brushing only lightly over it when the hunter wanted more. He whined piteously.

“Cas!”

“Or I could just lock you up and make you wear it when we go and see Sam tomorrow”, Cas mused.

Dean's stomach dropped. He wouldn't dare!

What was he thinking? The angel had him whipped with or without his mojo, and Dean knew it. Next thing, Cas would slot a vibrator in there and strap it inside of him.

“An interesting thought”, the angel purred, making Dean's stomach drop even further. “Perhaps later?”

And without warning, he suddenly pressed full down on Dean's prostate, making the hunter come with a shout, his body shuddering under the effort. It was definitely one of his top hundred orgasms, and he was sure only Cas' mojo prevented him from face-planting onto the bed afterwards. That and the finger by which, incredibly, Cas seemed able to support him.

“Food”, the angel said with an audible smirk, “and then more sex later. Fancy a piece of kale, Dean?”

Dean would have given him a filthy look, but he just didn't have the energy.


	18. December 17th

**Summary for the Chapter:**

> Baby, it's cold outside!

Door 17 opened to reveal – a plastic cup of water. What?

Dean picked it up and sipped it tentatively, but nope, it was definitely water. Fresh, too, not just tap water. As he wandered through the door, he wondered where Cas had gotten it from.....

Bloody fucking hell!

Well, the upside was that Dean was still dressed in his normal clothes. The bad news was that he was outside in the middle of an Arctic snowstorm, and the temperature was somewhere about minus way too much! The door, predictably, had vanished, but thankfully there was some sort of building not far ahead of him, barely visible through the almost solid veil of snow.

There was a cracking sound from somewhere, and Dean looked down. His cup of water was now a cup of solid ice – oh yeah, and he was standing there freezing his balls off like a loon! He stumbled forward, but even in the ten or so steps to took him to reach the hut, he could feel important bits freezing up. Thankfully the door was unlocked, and Dean stumbled through into a small single-room hut, slamming the door behind him.

Oh yeah, this was more like it. A blazing fire, which Dean could feel even from across the room. And the second-best thing; on the floor close to the fire was a pile of heavy blankets.

The best thing was Cas sitting up, naked at least from the waist up. Dean felt warmer already.

“You poor thing”, Cas said solicitously. “Come here, Dean, and let me warm you up.”

Dean nodded frantically and almost fell over his feet in his eagerness to reach the angel. 

“Hadn't you better get out of those wet clothes?” Cas asked.

Clothes. Right. 

That was where Dean's evening threatened to go south, because in his brief exposure to the bleak midwinter, his clothes had apparently somehow managed to freeze onto his body. He pulled hopelessly at his plaid shirt, and almost cried when it remained firmly stuck to his body.

“Cas?”

The angel blinked, and Dean found himself standing there naked, and still cold from his brief exposure. He scooted quickly under the blankets, and found to his delight that yup, naked down below as well. His own personal angelic hot-water bottle.

“Rather more, I hope”, Cas grinned and Dean tried to pull him even closer. “But let's get you warmed back up first.”

The hunter grinned, and wrapped himself right around his angel in a way that was totally nothing like a snuggle. Just like the noise that came out of Cas' mouth was nothing like a snigger.

Yeah, right!


	19. December 18th

**Summary for the Chapter:**

> Batman - sorta....

Dean opened Door 18, and a grin creased his features. A Batman badge? Perhaps he was gonna be Robin, and they would....

Down boy! Not yet!

Dean was still willing down his sudden erection when he walked through the door, and into a rather Spartan bedroom, contrasting rather oddly with the luxurious double bed. And regretfully he wasn't wearing the Robin costume, but instead something that looked like an old-time army uniform....

“Hullo, Private Winchester.”

Dean looked up, and Cas was stood leaning against the door opposite, dressed similarly except – obviously – as a superior officer. He was slowly undoing his beribboned top, and looking at Dean expectantly.

“Well?” he asked.

“What?” Dean said, confused. Cas smirked.

“A batman was a junior officer in the British Army, dedicated to serving his superior officer in any way the latter required”, Cas said with a smile. “Absolutely any way.”

Oh my god, he was wearing the tight white top! Dean was gonna die!

“Bed-warming, of course, was part of the job”, Cas said, removing his pants. 

“How do I....?”

“Just get in and use your body heat, private.”

Dean nodded, and quickly stripped his own uniform off before scooting under the covers. The bed was bloody cold, but he moved about as much as he could and it soon began to warm up. However, it meant he took his eyes off of Cas, until the latter coughed and Dean looked up.

Cas was wearing the brown leather holster. And nothing else! Dean would swear he felt light-headed as all the blood in his body turned around and made a dash for his lower brain.

The angel chuckled darkly, and Dean suddenly found Cas poised over him, his hands pressed either side of Dean's very willing body.

“Over!” Cas commanded, and Dean turned onto his stomach without even thinking about it. Only for the tease of an angel to then rub his cock up and down Dean's crack, teasing him mercilessly. The hunter thrashed about, but Cas easily held him down.

“Cas!” Dean whined.

“I think I am going to tease you like this all night, private”, Cas whispered, much to Dean's horror. “Pushing at your entrance, and then denying you the release you want. What do you think of that idea?”

With the holster banging against his thigh and Cas nibbling along his shoulders, Dean wasn't thinking anything – until without warning, Cas shoved in, and the hunter let out a triumphant “Yes!” as he joyously impaled himself on that holy cock. He had no idea how long it was until Cas reached round and lightly touched his own cock, but it was that that both made him achieve his own orgasm and, because even a hunter's body can only take so much, pass out.

God, he loved that sexy angel!


	20. December 19th

**Summary for the Chapter:**

> Dean likes shorts.

“Hell, no!”

The 'thing' that lay behind Door 19 was offensive, even when folded up. Unfolded, it was even worse; a pair of Bermuda shorts which seemed to have every color under the sun on them. The hunter sighed in a put-upon manner, but shucked off his clothes and donned the nightmare, before walking through the door to find.....

All right, perhaps the shorts weren't that bad after all.

He was very clearly on a beach lifeguard tower, with the wind blowing softy and the waves of an almost too blue ocean lapping against the shore. He barely noticed either, however, because Cas was standing there wearing an even more offensive pair of shorts than Dean, under an outside shower whose jets were bouncing off his angular torso. A mighty fine view, in Dean's humble opinion. 

Then Cas shucked off his shorts, and Dean decided that the view was now even better. He gracelessly almost fell over his own feet in his eagerness to reach the angel, who smirked as he stumbled forwards.

“Good thing I'm off-duty”, Cas rumbled, pulling Dean closer. “Love the shorts, by the way.”

“I hate them”, Dean blurted out, proud that he could manage a coherent sentence with most of the blood temporarily away from his brain.

“Indeed”, Cas said. “Then perhaps we had better see to that.”

Dean nodded excitedly, only for the tease of an angel to rub his hand up and down the outside of the shorts, making the hunter whine in anticipation.

“Patience is a virtue, Dean”, Cas smiled, squatting down in front of the hunter. Dean would have managed a swift and witty reply, but Cas kissing his way around the increasing bulge in the shorts made it rather hard. 

Make that very hard.

And now Cas was reaching his other hand up inside the roomy shorts, and teasing Dean's balls. The hunter's eyes watered.

“Cas!” he hissed.

The torture continued, Cas' finger probing at Dean's entrance but never quite pressing home. How Dean was remaining upright he didn't know; Cas must have been supporting him with his mojo, as both his hands were engaged in pushing him closer and closer to.....

Dean came with an unmanly yelp, coming inside the monstrous shorts as Cas withdrew his ministrations and placed his hands on Dean's thighs, supporting the hunter. He looked down in disapproval.

“Looks like we'll have to throw those shorts away now, Dean”, he said.

The hunter managed a weak grin. At least until Cas reached across to a box on the floor and produced a second pair of shorts, which looked even worse. But that was not what drew Dean's attention. The box looked to contain at least a dozen more pairs.....

Oh fuck!


	21. December 20th

**Summary for the Chapter:**

> There are no bees this time.

A blue headband. With two small black wings decorating the front of it. 

Right.

Dean stared at the item behind Door 20, then slipped it on and walked bravely through the door.... and into an open field. Still with the headband. But not his clothes.

Right.

There was some weird hippy music coming from somewhere, presumably the other side of the small haystack in front of him. Dean walked round the other side of it and.....

Right.

Cas. Sat there cross-legged in the cornfield, eyes shut and smiling serenely. Naked as the day he was born. Not even any bees around to hide his modesty.

Not that he needed to be modest, Dean admitted. He grinned, and went and sat down beside the angel. There was a considerable silence, before the hunter spoke.

“What'cha doin' Cas?”

The smile widened.

“We spend our existence, you and I, fighting the very worst the world can throw at us”, the angel said quietly. “I think that, sometimes, we need to stop and enjoy just what we are fighting for.”

Dean had a whole list of things he could think of doing with a naked angel in a field that were enjoyable. Sitting cross-legged in the sun wasn't on it. But he had to admit that it was nice, the two of them just busy doing nothing. He found himself shifting slightly to see if Cas was....

“Dean!”

Dammit!

“Maybe later”, the angel conceded with a smile. “And there's a barn over there with some rather conveniently-placed hanging ropes. We could re-enact our first encounter on Earth, where you were scared to death.”

“I was not!” Dean said hotly.

Cas quirked an eyebrow at him. Dean risked another pout before saying, “ropes?”

“You, tied up, for me to have my way with”, Cas said simply. 

Dean's eyes widened. Hot damn!

“Just don't stab me this time!”

“Hey!”


	22. December 21st

**Summary for the Chapter:**

> Dean gets knotted.

Door 21 revealed a handkerchief with a knot in it. Dean wondered if it meant that he was supposed to remember something, but he couldn't for the life of him think what. Puzzled, he walked through the open door.

Oh.

He found himself naked, face down on a (thankfully) comfortable large bed, with his wrists and ankles tied by (again, thankfully) soft ropes to the four corners. So it was like that, was it?

“Hullo, Dean.”

“Um, hiya Cas.”

He heard the angel move to the foot of the bed, and the sound of him removing his own clothes. Dean twitched in anticipation, only for Cas to pause.

“You know those fan fiction sites that you don't read, Dean?” he said casually.

The hunter scoffed into the pillow.

“Lot of nonsense!” he said firmly.

“I noticed that, among the stories which you seem to have 'inadvertently' saved to file, there is a preponderance of stories involving knotting.”

Dean's eyes widened. He wouldn't.....

Then Cas was pushing inside, and Dean momentarily lost the power of rational thought. At least until six foot of hunky angelic goodness was draped all over him, Cas nibbling along his shoulders.

“The choice is yours, Dean”, the angel whispered. “Remember, you always have the right to say no.”

“I'm a big guy”, Dean said firmly. “I can take it.”

Holy fuck! Cas' cock was suddenly swelling at its base, and Dean's poor prostate was right in the firing line. Part of him wanted it to stop, but most of him (led by Little Dean) was voting very firmly - very, very firmly - for it to continue.

And then Cas came, erupting inside the hunter, who roared his approval as his body just about gave up. He shuddered violently, which only caused the knot to rub against the rim, making his eyes water. He knew instinctively that Cas could make it go down in an instant, but he wanted this, being tied to his angel physically as well as emotionally. Cas was his!

“Well done, my beautiful hunter”, Cas praised.

Dean pouted.

“No fair!” he said, “complimenting me when I can't get away from you.”

“Indeed”, Cas mused. “I have you totally at my mercy for the next hour or so, Dean. Hmm, I wonder.....”

Dean's eyes widened when he realized just where Cas' hand was heading. Holy fuck......


	23. December 22nd

**Summary for the Chapter:**

> The angel is one teasing bastard!

A mobile. Dean checked it, but there were no messages on it or anything. He was still looking at it as he walked through the door.

He found himself in a large and dark hallway, in the sort of spooky mansion set-up that ghosts seemed to love, at least until the Winchesters rolled up. There were even cobwebs hanging from the distant ceiling. The phone beeped an incoming message, and Dean read it:

+I'm upstairs+

Dean grinned, and was about to start towards the stairs when a second message came through:

+Naked+

The walk suddenly became a run.

+Horny+

The run became a sprint. The hunter reached the top of the stairs, and groaned, Seemingly endless passages stretched away in either direction. He headed left, listening out for any clues (preferably heavy moaning). 

+Getting colder+

Dean almost fell over his feet as he did a 180 on the disgusting red carpet and sprinted back into the other corridor. A sound from behind one of the doors made him almost fall again in his efforts to stop, and he yanked the door open in triumph.

A black cat was sat there, looking balefully at him.

+I have your favorite dildo, Dean+

Slamming the door on the surprised feline, Dean bolted on down the corridor. And yes, the door right at the end was slightly open, and had a faint light flickering through the crack. Of course a Winchester knew better than to run unprepared into a room, but Dean was so desperate now that he didn't care.

+Inside me+

He threw open the door and ran through, falling onto the bed that was surprisingly close to the door.

An empty bed.

+This feels so goooooooood!+

Praying that the aneurysm didn't strike until he'd at least found the teasing bastard, Dean ran back into the corridor. He was about to start working his way back when a moan came from the door directly opposite him. He almost tore it off its hinges to get through it, and inside.....

+Found me!+

The phone hit the wall as Dean all but threw himself onto the bed, pinning the angel beneath his arms. Cas had worked that damned dildo right inside of him, and Dean determined to replace it with something, if not larger, then at least human. The angel groaned as it was worked loose, but the sighed happily as Dean pushed home, wrapping his oh-so-flexible legs around to try to pull the hunter in even further. Dean growled, thrust just twice, and came with a guttural snarl, before falling haphazardly on his angel.

His angel. Some day. Soon.

If he lived that long!


	24. December 23rd

**Summary for the Chapter:**

> Dean's lower brain makes an interesting decision - and lives to regret it!

Curiosity, they say, killed the cat. It certainly nearly did for Dean Winchester, who behind Door 23 found a folded piece of paper which stated, 'Do Not Open The Green Bottle'. Shrugging, he walked through the open door.

He was in some sort of laboratory place, because there seemed to be bottles of strange colored liquid everywhere. Cas was stood there in a lab coat, his back to the hunter, mixing a number of chemicals together, so Dean poked around the room whilst he waited for him to finish. And there, on the small side-table, was a green bottle.

He was Dean Winchester. Of course he opened it.

There was a warning hiss, and a jet of blue gas erupted from the bottle, forming a cloud around his head. Dean blinked in surprise as he breathed it in, and Cas looked up from his work without turning round.

“Dean”, he said warningly, “did you...?”

He got no further. Whatever was in that bottle got into Dean's brain in record time, and he leaped across the room, throwing Cas against the table and earning himself an angelic grunt. He yanked the lab coat up and the pants down, then pulled out his own suddenly erect cock and thrust straight in, coming the moment he bottomed out. 

Wow!

Except that, incredibly, his cock was getting hard again, and well, Cas didn't exactly seem to be making any objections, so Dean began to thrust into him a second time. This time he lasted a bit longer – nearly a whole minute, in fact – before hitting an orgasm that left him momentarily dizzy.

“Sex pollen”, Cas muttered from where his head was almost on the table.

“Huh?”

“You'll just have to keep going until it wears off, Dean”, the angel said nonchalantly, and dammit, he clenched his insides against the already hardened cock.

Dean began to have a bad feeling about this.

+~+~+

By six, he was painfully sore.

By ten, he could barely stand up, and Cas had to help him over to the bed in the corner of the room.

By fifteen, he was feeling dehydrated, and Cas insisted that he drink some water to recover. Fortunately the distance between attacks had lengthened to almost two minutes by this time.

By twenty-one, his body was lying uselessly on top of the angel's, whilst his cock kept on keeping on.

By thirty, he achieved a lifetime first – Dean Winchester wanted no more sex! Unfortunately Dean Winchester's cock wasn't quite done.

He passed out after thirty-three, but got woken up for the final seven goes by the one part of his anatomy that he now truly hated!


	25. December 24th

**Summary for the Chapter:**

> Argh, it's THAT word!

Christmas Eve had been very trying for Dean (especially as he was still exhausted from the forty orgasms the day before!), although the look of joy on that seraphic face had more than made it worthwhile. Inside Door 24 that evening he found a selection of Scrabble tiles, arranged to make 'D C LEUD'. Hoping that the angel had just misspelled the word 'lewd', he opened the door.

It was.... Cas' room. No special set-up, just the angel's room, with him sitting up in his bed. He looked up at Dean and smiled.

“Cas?” Dean said, confused.

“I see you did not put the clue together”, the angel smiled. “If you rearrange those letters into a single word, there is only on word in Standard English that you can make. A word that, I know, strikes fear into your very soul, Dean Winchester.”

The hunter puzzled over this for a moment before he got it.

“Cas!” he protested.

“The only thing you liked on those fan fiction sites more than knotting was the scenes of domestic bliss”, Cas grinned. “Especially - and yes, I am going to use the C-word here – when we cuddle!”

Dean folded his arms crossly. He was a manly man, and manly men did not cuddle. Ever!

Except that Cas was pulling out the puppy-dog eyes again! Now that was just unfair!

“Dean?”

“No!” He sounded like a petulant child, but dammit, he had standards!

“Please? For me?”

It took thirteen seconds for Dean to fold. Grumbling about what he had to put up with, he got undressed until he was in just his boxers, and got into bed, lying stiffly on his side. 

“I get to be the big spoon, all right?” he muttered, trying to revive his moribund manliness. 

“Maybe tomorrow”, Cas promised. “Tonight, it's my turn.”

Dean sighed as the angel folded himself along his back, tugging him closer. The hunter risked a pout, but relaxed, and was about to drop off when the angel spoke again.

“And also tomorrow, we may have Christmas Day sex”, he muttered sleepily. “Good night, Dean.”

The hunter stared into the darkness, now fully awake. 

“Cas!” he whined. “That was mean!”

There was a soft chuckle, and a nibble at the back of his neck. In fact, it was all rather ni..... tolerably pleasant, considering. Yes, he could still be a manly man and do the C-word thing.

Though he had a feeling that his manliness was just about to die laughing.


	26. December 25th

**Summary for the Chapter:**

> DTA - Dentist Trip Advisory due to excess fluff.

Dean loved the angel enough to buy him what he really wanted for Christmas, namely a promise of a trip to the rescue center in the new year to get a flea-ridden moggy. Even if it would be preceded by a trip to the drug store for copious amounts of allergy medicine. Cas told him he would get his gift later that evening, which of course left Dean in a state of high excitement all day. Especially as Cas insisted on wearing the panties beneath his often open blue dressing-gown.

The day was long and hard. So was Dean.

Door 25 lay in the middle of all the boxes, and Dean opened it tentatively. He wasn't sure what he expected to find there, but the contents succeeded in surprising him. It was the same throwing-dagger of Cas' that he had had on Day One of his adventures, what seemed like half a lifetime ago. Clutching it, he walked through to what awaited him.

Oh no!

Well, it was very obviously Heaven. The flowing ground-smoke and soft music was a clue, but a larger one was that this was his home, destroyed in the fire that had claimed the life of the woman currently gardening out the front of it. And the music was her favorite song, 'Hey Jude'. Dean bit back a sob.

“Mom?” he managed weakly.

Mary Winchester looked up, and smiled that familiar smile. It faded only slightly as her eldest son vaulted the fence rather than use the gate, and lumbered over the perfectly-manicured lawn to embrace her in a fierce hug.

“Hullo, sweetie”, she smiled at him.

“What's going on?” Dean asked, confused.

“Your new boyfriend asked me to bear witness to something important”, she explained. “He's standing behind you, by the way.”

Dean spun round so quickly he almost fell over, and sure enough, there was Cas, dressed in full angelic battle armor. The angel held out his hand, and after a moment's confusion Dean dropped the small throwing-dagger into it. Then Cas knelt down on one knee before the hunter.

Oh. My. Whoever is in charge up here now (please, not Chuck and Becky!).

“Dean Winchester”, Cas rumbled in his deep voice, “I have loved you the moment from when I gripped you tight and raised you from perdition.” The hunter grinned at the old saying, still hardly believing what was happening. “Will you marry me?”

The hunter was still standing there like a complete idiot, until his mother hissed his name, and he came back to life with a start.

“Yes!” he blurted out. “Hell, yes!”

“No mentions of hell, please”, Cas said with a smile. He folded his hand over the small throwing-dagger, and when it opened again, it had transformed into a pair of silver rings, each engraved with their initials. He gently took Dean's hand and placed the ring on his finger, then held out his own for the hunter, who reciprocated. 

“Kiss him, son!” Mary muttered, though she was smiling as she spoke.

And Dean did. He could even overlook his mother's “finally!” as she went inside the house.

Good things did happen, after all.

NOT QUITE THE END


End file.
